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With potassium carbonate; In acetonitrile; at 40.0℃; for 0.5h;Heating / reflux;
Preparation 194-chloro-2-morpholino-thiazoleTo a mixture of 2,4-dichlorothiazole (34 g, 0.22 mol) in acetonitrile (425 mL) add potassium carbonate (60.9 g, 0.44 mol) and then morpholine (21.2 mL, 0.225 mol) dropwise over 30 min. Reflux the mixture at 40 0C and then cool to 22 C. Filter the mixture and evaporate the filtrate. Triturate the residue with /-propyl alcohol (60 mL) at 22 0C for one hour. Filter the solids and dry under vacuum to a constant weight to afford the title compound (34.5 g, 76%). ES/MS m/z (35Cl) 205 (M+l)+.
With caesium carbonate; In tetrahydrofuran; at 110.0℃; for 3.0h;
Part B: 4-(4-Chloro-l,3-thiazol-2-yl)morpholine; In a sealed tube dissolve 2,4-dichloro-l,3-thiazole (1,00 g, 6.49 mmol), morpholine (1.13 g, 32.99 mmol) in dry THF (4 mL) and then add Cs2CO3 (3.17 g, 9.74 mmol). Heat the resultant mixture at 1 10 C for 3 hrs. Concentrate the reaction mixture in vacuo and treat the residue with dichloromethane (30 mL). Filter the insoluble material and evaporate the filtrate in vacuo to afford off-white solid. .H NMR (400 MHz, CDC13) 6.33 (1 H, s), 3.80 (4 H, t, J = 9 Hz), 3.45 (4 H1 1, J = 9 Hz).
at 20.0℃;
26a) 4- (4-CHLORO-THIAZOL-2-VL)-MORPHOLINE A solution of thiazolidine-2, 4-dione (0.5 g, 4.27 MMOL) and POC13 (2 mL, 21 MMOL} in CH3CN (20 mL) and 4N HCI/DIOXANE (1 mL) was heated to 70C overnight. The mixture was poured to the ice water and neutralized with saturated NAHCO3 then extracted by EtOAc. The organic layer was dried, concentrated and treated with morpholine (1.8 g, 21 MMOL). The mixture was stirred at room temperature overnight. The mixture was diluted with EtOAc and washed by water (3 x 50 mL) and brine (50 mL). The EtOAc phase was concentrated by reduced pressure and purified by silica gel chromatography to afford the product (126 mg, 15%). M+H+=205. 6. H NMR (300MHZ, DMSO-D6) 8 6.81 (s, 1H), 3.69 (m, 4H), 3.35 (m, 4H).
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